The Future Awaits
by lindsayd16
Summary: Dean wakes up in an unknown location to realize his worst nightmare has come true. Is it a result of the Mark or just his luck of the draw? Set after the season nine finale! Rated T for language.
1. Chapter 1

_Taking place after season nine finale_

** CHAPTER ONE**

_Man, my head hurts._

That was the first thought that had come to Dean's mind as soon as he regained consciousness. He remembered seeing Crowley and him saying something about going to howl at a moon but that was it. He felt something drip down the back of his neck and went to wipe it off when he realized he couldn't. Dean's eyes flew open as he took in his surroundings. His wrists and ankles were tied to a metal chair that was bolted to the floor. He looked around. _No windows, always a good sign_. He figured the door was on the wall behind him when there were no exits on either the three walls he could see. Just as he could feel the panic starting to sink in, he heard the door behind him creak open. Trying to look over his shoulder, someone ruffed up his hair and stood behind him.

"Show yourself you sonofabitch!" Dean spat.

Dean cringed as the person behind him laughed and grabbed a hold of his shoulders.

"Dean, Dean, Dean… You kiss your mother with that mouth? Oh… I forgot."

Dean's face paled and sweat formed on his forehead. He knew the laughter. He heard it often when he was in Hell. It still plagued his nightmares even to this day.

He made his way in front of Dean placing his hands back on Dean's shoulders and smirked. Dean couldn't believe it. He saw Sam kill him. _He saw it. _

"What? You aren't happy to see me? But Dean, we were so close. I thought of you as a son." The sarcasm was laced into his words as he took a step back crossing his arms across his chest.

"How…" Dean breathed still trying to get his thoughts in order.

"Let's not cloud this reunion with technicalities. The King of Hell thought I could be useful so he pulled some strings and here I am."

"What does he want?" Dean snarled.

"He wants to break you. Get that pesky humanity out of the way so the fun can begin." Alastair continued to laugh as he walked out the door leaving Dean alone with his thoughts.

...

_He was awake. He was safe at the bunker wrapped in his blankets. Granted, his pillow was soaked from how much he was sweating, but safe none the less._

_A dream. That's all it was. _

Dean groaned as he hauled himself out of bed only to be stopped by a sharp pain in his head. He touched the back of his scalp to feel a sticky substance coming from it. Pulling his hand back, he stared at it in disbelief. He glanced back at his pillows and low and behold, it wasn't soaked in sweat, but blood. Dean turned back to his hand and gasped when looking at his wrists to see rope burns.

_It was real. Alastair's alive and I'm so screwed._

_..._

He thought about yelling for Sam, but knew it wouldn't make a difference. Sam hadn't given a shit about him in months. Why would he care now? It was just something Dean would have to deal with, alone, as always. He rubbed absently at the Mark of Cain as he went to the bathroom to shower. Dean couldn't quite place it, but he felt a new sense of power in him. He felt stronger and ready to kill.

Sam jolted out of his state of hysteria when he heard the shower running. Had Cas come in the middle of the night? Drawing his gun he headed towards the now stopped shower. Just as he rounded the corner he saw a figure crouched over Dean's bed, hair dripping wet. Sam's eyes glanced at the now empty bed and the familiar build of the man.

"Dean…?" Sam whispered thinking it was a hallucination like the one's in his dreams last night.

Dean spun around; gun pointed directly at Sam only to be lowered just as fast once he recognized him.

"Sammy." Dean said with a smirk. "Miss me?"

But Sam still kept his gun raised. The only reason being was the now pitch black shade of Dean's eyes. This couldn't be happening. Not to his brother. Not to them. _We were just starting to be brothers again._

Dean looked puzzled. He put his hands up showing he meant no harm. "Everything okay little brother?"

"You're not my brother," was all Sam said before he shot Dean in the shoulder. Lucky for Sam, he had carved a devils trap into the bullet planning on using it on Crowley but he had never shown up. Dean cried out in pain as he fell to the floor gripping his shoulder. He looked at Sam with betrayal and confusion once he realized he couldn't move. He was stuck in the position he had fallen in.

Sam walked over to Dean drawing the angel blade and grabbed his collar, yanking him closer. "Who are you and why are you possessing my brother you son of a bitch!"

"Sam it's me! What the hell's the matter with you?! I'm not possessed!"

"SAM STOP." Sam spun around to see Castiel rushing in the room and grabbing Sam's arm. "It's him Sam. That's your brother in there."

Sam glanced back and forth from Dean and Castiel trying to make himself calm down. Cas then proceeded to drag Sam out of the room and closed the door behind them.

"That's not Dean."

"Sam, yes it is. The Mark of Cain… Had more of an affect then we originally thought it was going to have. The mark doesn't want to let go of him. It brought him back. His soul has been corrupted. I've never seen a soul as twisted as his is at the moment; it's even worse than yours was when it was pulled from the cage."

"So what are you saying Cas? That's he stuck like that?!" Sam practically screamed

"What I'm saying is that we need to figure this out. We can't help him if you have your head shoved so far up your ass that you don't realize how bad this is."

"We know how to cure a demon. Hell, we almost cured Crowley not even a year ago!"

"The keyword there is _almost._" Crowley appeared next to Cas in the hallway.

"You son of a bitch! You _knew_ this would happen!" Sam fumed lurching towards the King of Hell.

Crowley took a step back, hands raised. "Moose, do you really think I knew about this? I never lied to your brother. I only recently became aware of this alternate ending. But may I remind you two that Cain wasn't a normal demon. That little demon killing knife of yours didn't do a thing on Cain. Dean became a demon the same way Cain did, so I doubt any of the normal torture devices will work."

Cas nodded as if deciding what he was doing was right. "Then we need to find out. We will save Dean Winchester."

**TBC**

**Reviews are appreciated seeming as though this is my first story!**


	2. Chapter 2: Broken Toys

**CHAPTER TWO**

When Dean finally woke up, he realized he was sitting in a chair that was placed inside a devils trap. The bunker's dungeon still had the distinct smell of sulfur from when they were keeping Crowley locked down here. The bullet had been removed and his shoulder was bandaged up. At first he thought it was another dream, but knew how real it was when he saw Sam, Castiel, and Crowley standing in front of him. Sam's arms were crossed across his chest and Castiel looked so determined Dean couldn't look at him.

"Cas, do you have something you'd like to talk about?" Dean said with his usual sarcasm.

"You're a demon Dean. That's what I'd like to talk about." Cas said through clenched teeth.

Dean rolled his eyes surprised at the angles bluntness. "Not this again. Guys, I'm me!"

Just as Cas was about to say something else, Sam chimed in "Quit playing dumb. There's no way you don't know."

"Sam-"

"Cas I've been possessed before! You know when it's happening, trust me."

All of a sudden something snapped inside Dean. It was like the hold his humanity had gave out and the Mark side of him had taken over. It was still Dean in there, but it was the side of Dean he had buried inside himself that was running the show. The side that took over when he tortured in Hell and that helped him kill monsters in Purgatory. This Dean was cruel, unrelenting, and wasn't going to deal with the baby brother and an angel.

Dean's laughter filled the room. But not his normal light hearted laugh. It was the type of laugh that made your skin crawl. The eldest Winchester stood up doing a slow clap while trying to contain his laughter.

"Man, Sammy I did not give you enough credit when I was human. You really are the nerd I always called you. But, you do have one slight detail wrong. I'm not possessed, this is all me in here." Dean's smug smile was enough to make Sam snap. He tackled Dean sending them both to the floor and started throwing punches. In between each punch, the only thing that could be heard was Dean's laughter and Sam's occasional grunt. When Cas was finally able to haul Sam off of his brother, his knuckles were red and bloody. Dean stood up wiping some blood from his nose and smiled.

"That all you got little brother? You're rusty." Dean winked and with a flick of his wrist sent Sam flying against the wall. He then held up his other hand towards Cas daring him to move against him.

"This isn't you Dean." Cas said defiantly while looking down noticing Dean was out of the devil's trap.

"Isn't it though? Hell, I'm just surprised it hadn't happened sooner. After Hell and Purgatory, I should be a veteran demon by now. You knew Cas, you knew that it was going to happen eventually. But, like the good little angel you are you kept your mouth shut. Well look where it got you."

"Dammit Dean, we can fix this!" The angel pleaded. He couldn't lose Dean. He just couldn't.

"You can't fix something that's not broken." Before Dean could say anything else, the King of Hell decided to chime in.

"Not that this hasn't been fun, but we have a date." He said gesturing towards the new demon. "Hollowing at moons and what not. So if you don't mind-"Crowley snapped his fingers and they were gone. In an instant, Dean was taken away from Cas again. He wouldn't accept it. He would save Dean Winchester if it's the last thing he did.

Before he knew it, Dean was back on Alastair's rack. His wrists were clamped to a bar above his head that was too rusted for comfort. His feet dangled off the floor and he could see a cart full of multiple torture devices. He had remembered this very room from his first term in Hell and his eyes had to adjust to the dim lighting. Dean could hear the screams of all the souls around him. The difference this time though was that they didn't bother him. Every now and then he'd find himself smiling slightly which then caused the newborn demon to reprimand himself. _There's that humanity Alastair talked about. _The smell of sulfur occupied the whole room and Dean glared at the door waiting for someone to walk in.

...

**TBC**

**Thanks so much for all the nice reviews! I was so nervous putting the story up and the reviews made me feel a bunch better! Sorry this chapter is a little shorter, I was just too excited to wait until after work! More reviews are always welcome:)**


	3. Chapter 3: The Angst Has Risen

**Thanks so much for the great reviews! I hope I'm not updating too often.. If it gets annoying just let me know! The next two chapters will have more of Alastair in it!**

**CHAPTER THREE**

Sam was sipping a cup of coffee at the kitchen table for what seemed like an hour now. He had trouble finding the energy to do anything but research ways to cure demons and eat. Cas had just appeared and was staring intently at Sam, the worry lines in his face much deeper than they were yesterday.

"Sam." The angel said faintly.

Sam ran a hand across his face, trying to rub the sleep from his eyes. "Yeah Cas?"

"Have you found anything? Do you know where Dean is?"

"No Cas, I haven't found anything. Why don't you get some of your angel buddies to do some goddamn work and look for him?!" Sam hadn't meant to yell at Cas. He was just so worried about his brother. _Maybe if you'd paid more attention, you would've seen this coming. _Dean's voice echoed through Sam's head. Even though his brother had never said that to him, the thought was real enough to make him cringe.

The angel just frowned and left to go meet with his angels. Metatron had given him his grace back so he was able to teleport freely without feeling like he just ran five miles. The angel had work to do if he was going to get the eldest Winchester back safely.

…...

Alastair and Crowley were just about to walk in the room where Dean was held when Crowley stopped him.

"What are you planning on doing exactly?" The King questioned.

"I was planning on holding his hand and running through the wildflowers. Care to join?" A deadly smile crept across his face as he pushed open the door with the King slowly following.

"Well if it isn't my favorite customer. I gotta admit Dean, sure I figured I'd see you again, but never dreamed of it being this soon." Alastair said, a smugness in his voice, stopping inches from Dean's face.

"Dude you need a breath mint." Dean said giving Alastair a disgusted look. His comment earned him a punch in the ribs.

Alastair grabbed Dean's face with his one hand squishing his cheeks together. "I'd watch my mouth if I were you. Might make things go faster." Letting go of the new Knight of Hell's face with a shove, Alastair made his way over to his cart of toys.

Dean spared a glance at Crowley. For some reason, the King of Hell was silent. _Somebody pinch me, I'm dreaming. _

Alastair picked up a jagged looking knife that was as long as Dean's forearm. Dousing the thing in holy water and salt, the demon walked over to Dean and his now exposed chest.

"Let the fun begin." Alastair said with a sinister smile as he slashed the blade across the hunter's chest.

…...


	4. Chapter 4: Surprise

**Sorry these last two chapters have been kinda short. But, at least I uploaded them at the same time! Reviews are still greatly appreciated!**

**CHAPTER FOUR**

Dean was laughing. Not the sadistic laugh he had earlier, but the light-hearted laugh that only Sam and Castiel have ever heard. His eyes had switched back to that dazzling green color and even Crowley was trying hard not to crack a smile.

The knife didn't do a damn thing.

Sure it left a big gash across his chest, but it hadn't hurt the demon. Alastair had a look of bewilderment and awe as he slowly backed up from the Winchester. He mentally shook himself, and his bewilderment was replaced with a look of determination as he punched Dean across the jaw.

Dean spit the blood out of his mouth but kept his smile. "Guess I'll be a little harder to break then you thought."

"Oh Dean… That just means the more quality time we can spend together." Alastair turned and walked out the door with Crowley at his heels, hearing nothing but the soft laughter of Dean Winchester.

….

Crowley shut the door behind him just as Alastair shoved him against the wall. "Did you know this would happen?" he hissed.

The King of Hell pushed the demon off of him. "Of course not. But don't worry, I've got a plan."

"Which is what? Try every goddamn thing in the book?" Crowley could practically see the embarrassment of the knife not doing anything on the hunter radiating off of Alastair.

"Who would know better how to hurt a Knight of Hell, then a former Knight of Hell?" Crowley said like he was explaining it to a small child.

"You said your men hadn't found him yet."

"Not yet. But I have other… resources I can tap into." With that, the King disappeared leaving Alastair to his work.

….

Sam was in the middle of pouring himself another drink when the King of Hell popped up, almost causing him to drop the bottle.

"Hello Moose. Did you rob a liquor store?"

Sam shoved Crowley against the wall, placing the angel blade at his throat. "Where's Dean you son of a bitch!"

"Woah woah! Easy there Sam. I know where your brother is. But I didn't have anything to do with it."

Sam pressed the blade to the King's neck a little harder. "That's bullshit. You snapped your fingers and you two were gone!"

"The original plan was to help your brother with his new found powers. But… Alastair snatched him from me."

The hunter dropped the blade and backed away from Crowley. "No… No that can't be right. I killed him." Sam ran a hand through his hair. _I remember killing him. _

"Abbadon apparently thought he would be useful, so she brought him back. Now Alastair has Dean to try and squash the last bit of humanity that's left inside your brother. So, I brainstormed."

"And what pray tell, did you come up with?" The younger Winchester asked sarcastically, leaning against the table.

"I'm glad you asked." Crowley proceeded to then pour himself a drink. "I thought, what better way to understand a Knight of Hell, then another Knight of Hell?" Crowley smiled to himself at the thought of using the same line on Alastair. _If only they knew. _

"We have no leads on Cain. How are we suppose to find him?"

"Has that angel of yours all but vanished? Cain is only hidden from demons. I bet Castiel could find him in a second."

"Fine, I'll ask him." Sam said, sighing heavily. _This should turn out well. If Cain didn't like being found before, he sure as hell is going to be pissed about a second._

_…_


	5. Chapter 5: To Break A Winchester

**CHAPTER FIVE: To Break A Winchester**

"Castiel we need a leader!" Hannah practically begged the distraught angel. Now with Metatron locked up, all the angels had unanimously volunteered Cas to take over.

"Do you not remember the last few times I've played God? None of them turned out well. There are plenty of worthy angels to take the position." Cas said, willing Hannah with his eyes to understand. He couldn't do it. Not with Dean in so much danger. If something happened and he had to pick between the angels and Dean… He wouldn't put them through that again.

"But Cas-"Hannah tried once again to convince Castiel to help them. _We need a leader. Or we will crumple. _

Castiel cut her off, "I'm not doing it. I would like to be a regular angel. I will follow whoever you all appoint to be the leader. But for now, I have other matters to take care of." He had heard Sam's prayers for the last few minutes and couldn't ignore them anymore. Hopefully he figured something out about the eldest Winchester.

…

Alastair had his arms crossed across his chest, staring at the unconscious hunter. His head was drooped with his chin resting on his marred chest. Large gashes and small cuts were oozing blood and a small puddle formed at Dean's feet. Everything he tried only made the Winchester laugh. Except for the angel blade, nothing else worked, but all that managed to do was cause minor discomfort. He stared at the angel blade wedged into Dean's shoulder thoughtfully. Alastair walked over to his cart and grabbed two more. _Wake up sleeping beauty. _Alastair didn't want to give a single moment of peace to the hunter.

With that last thought, he drove the angel blade into Dean's stomach, up into his ribs. Dean's eyes flew open and he groaned slightly, but not nearly the reaction Alastair wanted. With a snarl placed on his lips, the King of Torture stabbed Dean in the thigh with his last angel blade. Looking over at his work and the three angel blades projecting from the Winchester's body, he stepped away feeling proud of himself.

"Is this as much fun for you as it is for me?" Dean said sarcastically. His eyes had stayed the normal bright green and he hadn't stopped smiling.

"Keep laughing, but once I find something that does hurt you," He laughed slightly with a cruel smile occupying his face. "Well… Let's just say you'll really have a reason to pray to that angel of yours."

Dean's eyes flashed black for a second before returning to green, but it was long enough to give Alastair a boost of confidence. An idea had sparked in his mind which he planned to get rolling as soon as possible.

…

Crowley was standing in the hallway waiting for Alastair to walk out. He wanted a progress report but didn't want to interrupt anything, disturb him while he was at work. He had only been waiting for a few minutes before the demon finally walked out closing the door firmly behind him.

"Anything? Anything at all to wipe that smug smile off his bloody face?" Crowley practically spat. Even though he had grown quite a liking to the eldest Winchester, his cockiness was starting to get the best of The King.

"Nothing works. The angel blade only causes a slight irritation, like a bug bite. Nothing else does a fucking thing."

"I've got the angels busy on lookout for Cain along with Sam. Hopefully that'll give them enough distraction to not be looking for you or Dean." Crowley said leading Alastair to a room down the hall. "Come, I'd like you to meet someone."

Opening the door, it was the same setup as Alastair's rack, but with a new host occupying the restraints.

"Tell me, are you bored with your latest chew toy? Or would you like a new one?" Crowley asked, gesturing to the unconscious body.

Alastair just smiled as he strolled into the room, glancing at Cain with a disgusted look. _How did he let Crowley of all people catch up to him?_

….

"I'm here Sam. What have you learned about Dean?" Castiel said, appearing next to Sam's hunched over form at the kitchen table. The bunker had the stench of alcohol permanently burned into it from the two brothers combined. _They need a new grieving mechanism. _

Sam groaned and looked at Cas, blinking away the haze the alcohol left on his vision. "Crowley wants us to find Cain. Something about him being able to help."

Cas's eyebrows scrunched together in thought. _Why are we trusting Crowley all of a sudden? _"Um… Sam. Isn't Crowley the one who took Dean?"

Sam cringed. "No. It was Alastair, according to him at least."

Castiel thought about this for a moment before vanishing. He returned a few moments later with a look of aggravation. "Cain's in Hell, along with Crowley _and_ Alastair."

"That was fast. Wait, Crowley's with him?"

"Correct. I think you've been lied to Sam."

"Lied to about what?" Crowley asked, who appeared sitting on the counter.

"Nothing. Anything on Alastair?" Sam said a little too quickly.

"No, anything on Cain?" He retorted.

Sam avoided eye contact before Crowley finally disappeared.

Sam looked over to Cas with a look of determination. He was going to save his brother and he knew the angel would be more than willing to help him.

"I need a two way ticket to Hell."

…...

It was quiet; and for Hell, that was scary. He hadn't seen Alastair in a solid two hours and was beginning to worry what the demon was up too. Dean's eyes had faded back to black as he was struggling to keep his humanity in check. He couldn't let it be completely loose because then he would be worried about Sam and Cas.

_Sam._

He hoped his brother wouldn't find him. He knew Alastair would just use Sam as leverage against him. But, he knew that Sam would try his damndest to find out what the hell happened to his older brother.

_Unless he stopped caring. He already told you he wouldn't save you. _The thoughts penetrated the hunter's brain, causing him to cringe.

Dean could feel his humanity slipping. He wouldn't let Alastair or Crowley win. Somehow he had to keep himself from losing his hold.

He looked at his surroundings and glared at the angel blade in his stomach. Dean tried to fight the restraints but they were too tight and too strong for him at the moment. _I need time._ How to get said time, was what kept Dean's mind reeling.

….

**TBC**

**I can't tell you guys how much I love the reviews and that you guys actually like my story. To be honest, I didn't think anybody would. If you have any specific things you think I need to fix, please tell me so I don't keep doing them! Any other ideas/suggestions are welcome!**


	6. Chapter 6: Barging In, Bullets, Blazing

**CHAPTER SIX: Barging In, Bullets Blazing**

"Sam, maybe that's what they want, to lure you down there to use you as leverage against Dean!" Castiel was done trying to use logic. The damn Winchester was just as hard-headed as his brother and his mind was made up.

"I have to do this. I'm not letting him rot down there again! Now, you can come with me and help, or I'll find some reaper to get me down there." Sam had gone to his room and was packing a duffel bag full of the essentials he'd need: bullets with devils traps carved into them, salt, holy water, ruby's knife, and an angel blade. Hopefully, all of this would be enough to get Dean home safe.

_If he's still alive. Or still wants to see you. _

Sam tried to banish the harmful thoughts as he shoved past Cas into the hallway.

"Sam wait! Let's at least come up with a plan before you go in there half-cocked like usual. We have one shot at this."

So Sam stopped and decided to listen to the angel. He needed Castiel's help so he might as well listen to the guy.

…...

Alastair walked out of the room that Cain occupied, unsuccessful once again. _Damn Knights of Hell, fucking invulnerable to damn near everything. _

He made his way into the room where Dean was to find Crowley admiring his handiwork and the hunter glaring at Crowley with pitch black eyes. Alastair could almost see the steam radiating of his new pet.

Crowley turned around and smiled at Alastair, "They're on their way. I told you they didn't trust me."

"Who? Who's coming?" Dean demanded. He was so done with Crowley and his vague ass statements. For once, he was going to get answers.

"Are you really in a situation where you can demand anything?"

"Crowley I swear to god I'll-"He was cut off by Alastair's laughter.

"Last time I checked you were a little busy Dean. I don't think you'll be doing much of anything for awhile."

"You should at least tell me who's on their fucking way!" Dean growled. He was pissed. He could feel his humanity ebbing away but didn't care at the moment. He wanted answers.

"Your Calvary. Who else would march down to Hell to save your sorry ass?"

With that one sentence, Dean's eyes faded back to green. His humanity was front and center and he was panicking. _No no no. They can't be coming. Dammit Sammy why couldn't you just leave it alone?_

_…_

Sam and Castiel appeared in a dark hallway covered in blood from floor to ceiling. The smell of rotten flesh penetrated their noses causing the young hunter to gag. Sam lifted his arm to cover his nose as he made his way down the hallway, gun in hand, with Cas shortly behind him. The angel put his arm out in front of Sam, motioning for him to stop. He took out his angel blade, peaked around the corner, and stabbed a demon in the throat. _Smart choice to bring the angel._

They made their way farther and farther into the deepest parts of Hell when they came across a hallway lined with doors. Peering inside of a couple, Castiel noticed they all had different racks in them, with different people restrained.

"Dean must be in one of these. You search that side." Cas said, moving to the opposite side he told Sam to look at.

After what seemed like 20 different rooms, Sam's breath caught in his throat. In a mere second, Castiel was next to him looking in the window that was on the door. The angel's heart broke as he saw the shape Dean was in. He was about to open the door when Sam grabbed his wrist stopping him and pointed at Alastair who was now blocking the view of Dean.

Cas twirled the angel blade that was in his hand as Sam loaded his gun with devils traps carved into the bullets and put Ruby's knife at easy access. With that, they burst through the door.

…

Alastair was facing his cart full of knives and whatnot. He had just finished unbuttoning his shirt and to put it as an understatement, Dean was a bit freaked out.

"Listen man, I don't really roll that way. What you and Crowley have is none of my business, but please, leave me out of it." Alastair ignored Dean's sarcastic comments as he began to carve some type of enochian symbol that the hunter couldn't quite see. When the demon finally faced Dean, he flinched.

"Recognize it? The second your feathered friend walks through that door he'll be sent back to god knows where. It'll buy me some time to really get some work done." Alastair said with a hint of pride in his voice.

"You really think they're dumb enough to burst through the door? Come on, I know my brother and he'd have a better plan then that."

"We'll see won't we? Either way, you won't be getting off my rack anytime soon." Alastair moved to stand in front of Dean and grabbed the angel blade that was protruding from the hunter's shoulder. He stared right in the black eyes of Dean Winchester and twisted right when Sam and Cas busted the door open.

"_DEAN." _Sam yelled. He barely had a chance to adjust to his surroundings before Alastair had turned around, placed a hand on his chest. A flash from a bright white beam sent Cas packing. _There goes my back up. _

"Sam, so good to see you again. It's been awhile." Alastair flung the youngest Winchester up against the wall, sending his gun flying. "Tsk tsk tsk… Coming in right through my front door was a really unfortunate battle strategy. Your brother thought more from you."

"Alastair don't you dare touch him you son of a bitch!" Dean's eyes couldn't get any blacker. He yanked at his restraints trying to get to Sam. _I can't let him die because of me. Again._

The demon slowly made his way over to Sam, eyeing him like he was the long lost treasure he'd been seeking. "I finally found your brother's Achilles heel."

The realization that both he and Sam were screwed finally hit Dean. He was out of time; and out of options.

….

**TBC**

**Hopefully this chapter didn't suck? I feel like it did. Anyways, Crowley and Cas will be coming back next chapter so don't worry! Will Dean save himself and Sam? Who knows. I don't even know yet. We'll see how I feel when I write it. Thanks so much for all the support and I hope you're enjoying it? Maybe just a little?**


	7. Chapter 7: When All Is Lost

**CHAPTER SEVEN: When All Is Lost**

Dean was pissed. Not his normal kind of pissed either. He had the whole nostrils flaring, black eyes, eyebrows creased look going on. It was all focused on Alastair, which should've scared the living shit out of him. But all Alastair managed to do was laugh.

"You know Sammy; your brother isn't still in there." Alastair said matter of fact, grazing the hunters chin with a knife. "Well, maybe there's a shred of humanity left, but nothing to keep your hopes up for. I mean, for fucks sake, did you really think you could save him? Have you not been paying attention for the last year?"

All Sam did was glare at Alastair. He didn't want to give the demon any satisfaction by replying. The younger Winchester stole a glance at his brother and he felt a pang of guilt. _He let this happen, if only he had gotten to him sooner; cared a little more. _

Crowley appeared standing next to Dean, one hand in his pocket. "Moose, pleasure as always."

"You son of a bitch, this was a trap!" Sam hissed

"I'm sorry, what?" The King said as he grabbed a hold of the angel blade in Dean's shoulder and twisted it. Dean let out a small groan, but nothing too worrisome.

Sam was fuming. Before he had time to respond, Alastair plunged the knife into the youngest Winchester's forearm. He screamed in pain as Alastair jerked the knife downwards.

It all happened so fast that Dean hadn't processed what he did until he realized his hand was stuck in Alastair's stomach. Pulling his hand out, he was smiling. Sam looked over at him not being able to recognize the figure with his hand covered in blood. It wasn't Dean. It was black eyed and laughing at the thought of Death and blood. Alastair's body crumbled to the floor, but they all knew he wasn't dead.

Dean's last shred of humanity had shattered.

…

It had been a week since Sam had seen Cas, Dean, and Crowley.

After Alastair's body had folded in on itself on the floor, Dean winked at him, snapped his fingers, and was gone. Crowley fled soon after.

Ever since Alastair had sent Castiel back to who knows where, he hadn't shown up since. _Maybe he's dead, like your brother. Can you manage to keep anyone around you alive?_

But Dean wasn't dead, not really anyways.

The youngest Winchester was in the middle of looking through a book of spells when Castiel appeared behind him looking like complete shit.

"Sam, what are you doing?" The hunter jumped not noticing Cas's presence.

"Cas, man, I thought you were dead." Sam then pulled the angel into a tight embrace, smiling when he returned the hug.

"Alastair's spell was stronger than one's we have encountered in the past. I was just an hour ago strong enough to stand on my own. Now, what happened?"

Sam then relayed the whole horrifying experience for his friend. When he was finished, he gestured toward the book he was reading. "I was trying to find either a location or summoning spell for Dean. Maybe if I got him here or went to him I could…" _He could what? Bring his brother back from the deep hole he had gone in? _

"Dean is not lost. I'm sure of it. As of his whereabouts, I am unsure. Let me know once you find some type of spell that could benefit us. For now, let me see what I can gather." Cas then disappeared, returning a few moments later. "That was interesting."

"Did you find him?"

"No, there is not a single trace of your brother in the U.S. He must've warded himself from angels." Cas muttered some profanity under his breath that he no doubt learned from Dean.

"What about this?" Sam had his finger on a spell, showing Cas to see if it was possible to work.

"It may. We could always try it."

…

"Crowley, good to see you." Dean said a little too sarcastically. He appeared in Crowley's office, which resembled the oval office except much, much darker and with more blood. He crossed his legs on top of the King's desk as he gave Dean a disgusted look.

"What? Did you lose your manners along with your humanity?" Crowley stood up from his swivel chair and shoved Dean's legs off his desk, dusting it off before leaning against the desk. Staring at his new Knight, he reached behind him and poured himself a drink.

The Winchester rolled his eyes as he sat up in his chair. "You rang?"

"Yes. Where the hell have you been?"

"I've been busy." Dean spat, he hated being pulled away from his 'work'.

"I'm gonna need a little more information than that."

"Why's it any of your fucking business? In case you haven't noticed, I'm not one of your demon bitches. Just because I lost my humanity doesn't mean I'm not a part of Team Free Will." He said with a smirk.

"Watch your tone with me-."

"Or what?" Dean laughed his cruel laugh as he stood up. "Have you failed to notice that I'm a bit out of your league?" The demon towered over Crowley, daring him with his pitch black eyes to try something. "I don't answer to you, and don't have to come when you call. Let's get this straight now; if I thought you were worth my time, you'd be dead by now." With that, Dean was gone.

Crowley ran a hand down his face, wondering what the hell he had brought into the world.

….

Dean didn't know where he was, but he didn't care. He was more focused on the screaming girl at his feet.

He had gone to the bar the night before, trying to find someone to calm his need to kill. Unfortunately for this girl, she was it.

After getting her back to his motel room he had gotten before he went out, he did what he normally did when he brought girls back from bars. After a night of passion, she awoke tied to a chair and gagged.

The Knight of Hell had spent hours torturing her. He was finally starting to really enjoy himself when he heard the obnoxious mini earthquake signaling he was being summoned. Dean went on with what he was doing, not actually thinking it would work.

…...

After gathering all the supplies, Sam and Cas stood in the bunker's dungeon. The hunter just finished reciting the spell when he threw a match in the flame. To all of their surprises, Dean showed up in the middle of the devil's trap.

Every inch of the eldest Winchester was covered in grime and blood. He wore his black t-shirt with torn jeans as he looked at the pair in utter disbelief. Dean was still holding a knife that was dripping with fresh blood. "How in the fuck…"

Nobody knew what to do because none of them expected it to work.

The silence was interrupted by Dean clapping with a menacing smile on his face "Well congratulations. You found me. Now what was your big plan?" He said as he walked out of the devil's trap. He decided not to attack them yet, he wanted to toy with them first.

"Dean, I know you're in there somewhere. You just have to keep fighting man." Sam said out of desperation.

Dean rolled his black eyes as he pulled up a chair, taking a seat. "So I'm going to go with you have no plan?" He smirked as he wiped his bloody knife on his jeans. "I was in the middle of something important. I really hate to be interrupted." Dean glanced up at Sam noticing how much like shit he looked, and smiled in satisfaction.

"Mind if I try something?" Cas said pulling out the demon warded handcuffs. "I'm curious to see if these work."

Dean raised an eyebrow, surprised at the angel's genuinely curious tone. He smiled putting out his hands, "If you need to try it to help you sleep at night, who am I to stop you." Dean didn't know at the time, but Castiel had conversed with Cain learning a few new sigils that he had carved into the cuffs.

Approaching Dean, Cas quickly put one of the cuff's on Dean's right wrist only to have Dean shove him away. The demon winced as he felt his power diminish by half. _What the hell? _Sam ran behind Dean, pushing him back in the seat by his shoulders as Castiel ran back up cuffing the other wrist. All of a sudden, Dean's smug smile vanished as he realized how screwed he really was.

Sam came around in front of Dean, reciting the same word's he had said to Crowley a year ago:

"You're ours."

….

**TBC**

**I love all of the nice reviews. You guys are great(: Hopefully the story is developing nicely. If you guys have any suggestions I'd love to hear them!**


	8. Chapter 8: One Last Chance

**CHAPTER EIGHT: One Last Chance**

"Man, it is just not my week, is it?" The demon asked with a smirk.

"It's about to get worse. Trust me." Sam said, with a hint of regret in his voice. _Poor Sammy, so worried about hurting his big brother._

_"_You wouldn't hurt me Sam, be honest with me at least. You'd just be picturing the old me and probably start sobbing or whatever else sappy shit you like to do." Dean rolled his black eyes.

Sam knew deep in his heart that he couldn't hurt Dean. But him and Cas had already talked about it and the angel offered to do most of the work. At the moment, Castiel was putting the final touches on his plan.

"Sam, can I ask you something?" Dean's eyes switched back to that bright green color and he looked like he was genuinely curious about something.

So Sam bit, "What could you possibly have to ask me?"

"Will you undemon proof my car for me? I gotta admit I miss my baby." His brother was smirking. God, he hated that look on his face.

The phrase was so Dean- like (except for the demon part) that Sam's heart ached.

After what seemed like a decade, Castiel walked into the room with his hands in his trench coat pockets. He looked at Dean with frustration.

"There's my favorite feathered dick. You know Cas, if your face stays in that position for too long, it'll get stuck that way." The demon said with a sly grin.

"Are you really not worried Dean?" Castiel said leaning his head down so their noses were inches apart.

"About what you two might've come up with?" He laughed, "No, if Alastair couldn't find anything, I'm doubtful you two pansies did."

"Don't be so sure. Alastair doesn't have nearly as many friends as I do." The angel looked so damn confident, Dean wavered.

"You can't hurt me." Dean said with a shaky laugh. The cuffs had made him feel so powerless. He was actually scared, which he didn't even remember feeling ever since he changed. The hunter knew that in order to get out of this one, he'd had to be pretty damn cunning.

"We'll be getting there. Don't worry." Castiel said as he crossed his arms. Dean could see the angel was having an internal struggle at the moment. His brows were creased and he had a look of concentration. Sam on the other hand just looked tired. _If I'm such a bother why don't you just let me go? _

Dean smirked, "Are you going to cure me now? Is that it? Well fellas, I hate to break it to you, but I sincerely doubt it'll work."

"See, we thought that too. But then the summoning spell worked and so did the cuffs. Things are looking up." Sam said casually like he wasn't just talking about putting his brother through excruciating pain as they try to heal him. Cas had told him in the hallway before they attempted this that he had a plan but had refused to let the youngest Winchester in on it.

Castiel walked a little closer to Dean, "I had a really good conversation with Cain."

"Did you now?" Dean said, looking up at him with fake interest.

Cas smirked, "He tipped me off on a possible way to hurt you. I planned on trying it out."

The demon had noticed a change in Castiel. Instead of being the innocent puppy dog he normally was, he was hard, sarcastic, and so much like Dean it was a bit like looking in a fun house mirror. He smiled at the thought of how much influence he had over the angel. A prickle of panic scratched at the back of Dean's mind. He tried to imagine what in the hell Cain could've told him.

"Dean?" Sam said, looking at him, worry in his eyes.

"Oh sorry, I was fantasizing about different ways to kill Cain. You were saying?" The angel and Sam then approached him, and secured his wrists and ankles to the chair with chains, not trusting the strength of rope. Moving beside Dean, Sam cleaned a spot in the crook of his elbow with a wipe.

"What the fuck are you doing?" Dean glared at Sam while trying to move his arm away. He hadn't noticed before, but there was an IV bag hanging from a stand next to him. Attached to the IV, was a bag of blood. The demon could tell it wasn't human, but from what had the blood come from, he wasn't sure.

"Hey!" The eldest Winchester said when Sam stuck a needle in his arm and then secured it to the tube from the bag. Bending the tube, he kept the blood from going into Dean's vein.

"Figured it out yet?" Castiel asked, angling his head a bit. "It's the purest of them all. We need to cleanse you before the real curing can start. Who knows how long this could take. Let's just say, it might be a painful few days for you."

The connection finally formed in Dean's mind. _Angel blood. _But would it work? The demon was almost positive it would, with his luck. Cas saw the recognition on Dean's face and smirked at him with satisfaction.

"You need to cleanse me? This is rich. Come on guys, why would Cain tell you anything to hurt me?"Sam could hear the panic in Dean's voice. His brother was desperate, scared even. It was almost enough to have Sam pull the IV out and unlock the cuffs. Almost.

"I simply explained to him how out of control you were. He was more than happy to assist me. But because you aren't a normal demon, we have to get your blood to a more… lower class demon type before the actual curing can happen." Cas backed away and nodded at Sam to let go of the tube.

But Sam hesitated. He would be hurting his brother and he didn't know if he could do that again. Finally, Cas went over, took Sam's hand, and released the tube letting blood flow freely into the demon's arm.

...

**TBC**

**Thanks so much for reading! It really makes my day! Will the blood hurt Dean? Can Dean be cured? I'm as curious to find out as you guys.**


	9. Chapter 9:

**CHAPTER NINE: When Faced With A Difficult Question**

Sam was sitting at the long table on the main floor of the bunker with his head in his hands. He was hunched over with his elbows on his knees, taking deep breaths.

None of them had slept last night. Dean was up all night screaming, who would've thought the angel blood would work this well? Sam was up all night listening to his brother screaming and not being able to do anything about. And Castiel, well, he didn't sleep.

"Here," Cas said nudging a cup of coffee in Sam's face. The youngest Winchester took it, but didn't take a sip. "I'm going to go down there and evaluate how much progress has been made."

Sam moved to get up but the angel just pushed him lightly back down into the seat. "No, you stay here. I can handle Dean." The hunter nodded in appreciation as he watched Cas make his way to the stairs.

…

Dean heard the door creak opened and tried to guess who it was. By the light pitter patter of footsteps, he guessed Castiel. Sure enough, the angel yanked the shelves out of the way, and walked in.

Last night had been excruciating. Dean had never experienced pain like that before. It was like someone had stuck a hot, rusty knife into his stomach and constantly kept turning. The last of the blood from the IV bag had flowed into the demon's blood stream, and he was breathing hard. Somehow, through all of the screams, pain, and desperation, the eldest Winchester's new trademark smirk was firmly placed on his face.

_What a dick. _Castiel couldn't help but think. How in the hell was he still up right, let alone smiling?

"Someone's in a good mood." Castiel practically hissed at Dean.

The Knight of Hell laughed, "You know, you and Alastair have a lot in common. He thought it'd be easy to break me too. Guess you both shouldn't be so overly confident. You know what happened when Alastair got too cocky. It'd be a shame if the same thing happened to you." Dean's smirk only deepened.

The smugness in his voice is what caused Castiel to stop playing games. "In case you haven't noticed, I'm not some dick demon. Trust me when I say this Dean Winchester, I will save your sorry ass if it's the last thing I do. I'll be damned if I raised you from perdition for nothing." With that, Cas punched Dean right in the jaw.

Spitting out blood, Dean just shook his head. "Was that you?" He said, nodding at the empty IV bag.

"Yes." The angel said flatly. He pulled out a fresh bag from his inside trench coat pocket, and walked over to the stand.

Dean took a sharp intake of breath, eyeing the bag like it'd bite him. "This is pointless."

"Maybe, but at least I can say I tried."

Castiel turned and walked out, unable to hear the sound of his own thoughts over Dean's pained screams.

….

The second Castiel had left Sam alone; Crowley came out from hiding behind the corner. The youngest Winchester barely glanced at him before getting up and leaning against the table. After running a hand through his hair, he crossed his arms.

"You have something of mine. I'd like it back."

"Oh, you mean Dean? Yeah sure let me just go put a bow on him for you." Sam rolled his eyes, picking up an angel blade from off of the table.

"Moose, can we at least talk about this? Obviously you guys aren't getting anywhere with him. I was making progress."

"Yeah, in the opposite direction of where he needs to go."

"Since when do you know what's best for Dean? Last time I checked, I was with him more this past year then you have been in three." Crowley put his hands in his pockets, trying to figure out a way to get by the Winchester without hurting him. Just in case they had gotten somewhere with Dean, he didn't want him to hold Sam's death against him.

Before Sam could make a witty remark, they were both caught off guard by Dean's screaming. A few seconds later, Castiel strolled in.

"Anything?" Sam asked his tone full of hope.

The angel just shook his head and turned his attention towards Crowley. "Why is he here?"

"Simply to collect what's mine." The King stated. "I brought him back into this world; therefore I have a right to him."

"He's not some damn property for you to possess!" Sam spat. He was tired of Crowley's bullshit.

Crowley burst out laughing. "Isn't that the pot calling the kettle black? I highly doubt Dean is up there willingly. If I had to guess, he's tied to a damn chair. So if he's not mine to possess, why is he yours to?"

That stopped Sam. _Who was he to decide what to do with Dean? But if he just let him lose, he'd have to kill him, or some other hunter would._

"We're trying to help him." Cas argued.

"So am I. Helping him control his powers will be more successful then trying to cure him." Crowley rolled his eyes at the lack of logic the angel exhibited.

All of a sudden, Crowley took off running. No joke, he was literally running down the hallway towards the dungeon. Not even five seconds after the King had taken off, Cas and Sam were following. He wouldn't let him have Dean. Not again, not after what happened last time. Castiel then tackled Crowley to the floor, just outside the door. Sam ran inside and barricaded the door shut. Rummaging through the shelves, he managed to find a can of paint. He then proceeded to draw a demon warding symbol on the door to keep Crowley out, and ultimately, Dean in.

…...

"Please don't tell me, you three didn't just _race _down here." Dean was laughing, _really _laughing. Sam had only heard this laugh on occasion, but hadn't heard in at least three years.

Sam stared at the demon in disbelief.

Dean stopped as fast as he had started. He blinked in confusion, not sure himself what had just happened. "No no. This can't be happening." He whispered.

Sam sank down against the wall, landing on his butt. He figured he'd be in here awhile. Hopefully his brother wouldn't run his mouth.

But unfortunately, that was false hope.

"So, Sammy, looks like we have some quality time to spend together, tell me, should we join hands and share our deepest feelings?" Dean's words were laced with sarcasm. He was trying to cover up the effects the angel blood was having on him, but Sam knew better then to believe it wasn't staged.

The youngest Winchester looked up to see that the blood bag was empty already. Glancing around, he didn't see anymore. _Great, now there's nothing to keep his mouth shut. _

"Did I ever tell you how handsome you look when you scowl?" Dean said, winking at his brother.

Sam hadn't even noticed he was scowling until the demon had mentioned it. The hunter stood up slowly, taking a few steps towards Dean. "Why did you let this happen?" The question had been itching at the back of Sam's mind ever since he saw Dean's black eyes. _Why did you do this to me? _He knew it was selfish to think, but he couldn't help himself.

"Last time I checked, you said you wouldn't save me. So I'm slightly confused why I'm in the situation I'm in. If you really didn't give a fuck about me, I would still be on Alastair's rack. Yet, here we are."

"Come on Dean, you really couldn't tell I was lying?! You really think I wouldn't try my hardest to save you? Sure, I wouldn't go as far as angel possession, but I would still try!"

"But torturing me is so much better?" Dean scoffed. "That's great. For fuck's sake Sam, at least I didn't try to kill you myself. All I ever did was my job, protect little old helpless Sammy." He smirked at the end.

Sam couldn't think of a reply. It was their Dad's fault for cramming that down his brother's throat, not his. But Sam still blamed Dean for it, all of it. Now he was torturing the one person who ever cared enough to die for him. The hunter put his hand in his pocket, rubbing his thumb over the handcuff key. He looked over his shoulder at the still locked door and thought, would letting his brother go really be the worst route to go?

Sam strolled over to Dean and undid the chains. He carefully removed the IV from his brother's arm, but kept the cuffs on.

"You're serious? You're letting me go?" The eldest Winchester raised a curious eyebrow at his torturer.

"Not quite." Sam grabbed a hold of Dean's arm and dragged him to the door and opened it. He quickly grabbed the paint and made a huge X through it with his fingers. Castiel and Crowley were gone, so the hunter dragged the demon down the hallway to the garage.

"Where the fuck are we going?" Dean spat. There was a slight hint of worry in his voice, but he masked it the best he could. Approaching the Impala, Sam shoved his brother into the passenger side and took another pair of regular handcuffs from his back pocket. Attaching one cuff to the chain of the demon warded cuffs, and the other to the inside car door handle, Sam shut it and climbed into the driver's side.

_What the hell am I doing? _Sam thought as he started the ignition and left the safety of the bunker with his demon brother.

…

**TBC**

**How was this chapter? I was a little worried about uploading it because it seemed… I don't know. Either way, please continue to leave such nice reviews. Hopefully you are still enjoying the story!**


	10. Chapter 10: On The Road Again

**CHAPTER TEN: On The Road Again**

They weren't even ten miles away from the bunker before Sam had truly realized what he had done. He glanced over at his brother only to see Dean was staring at him, brows furrowed.

"What?" Sam snapped, he had just saved his ass from torture and yet he was looking at him like he was deranged.

"I'm just a little curious as to what the fuck you're doing? Last time I checked I was some douche bag demon who needed to be locked up." Dean was still staring at his brother, making sure he hadn't lost his mind.

Sam shrugged like it was no big deal, earning him an eye roll from the demon. "I didn't think we were taking the best course of action." The youngest Winchester said, sounding like he just pulled it out of his ass.

"So really you have no idea?"

"Not a clue." Sam said sighing.

"No that's good, great plan. Oh wait, now we have a pissed off angel, a possessive demon, _and _most likely Alastair on our asses. No, this was a terrific plan." Dean's voice was full of sarcasm as he turned his head to look out the window. "Can I drive?"

"I haven't lost my mind Dean. Nice try though." Sam said as he let up on the gas a little. He hadn't realized he was going around 75 mph as they drove down a country road.

_We are so screwed. _Sam thought, looking in the rear view mirror.

…

After tackling Crowley to the floor, Castiel had teleported them both to an old motel room about 50 miles away from the bunker.

They were both glaring at each other, breathing hard. The King made his way over and sat on the bed that creaked under his weight.

"Really Cas? Really?"

"Don't call me that." Castiel said as he looked out of the window. He assumed Sam would do something to insure Crowley couldn't get into Dean.

"Can't we be reasonable here? You know he's destined to go demonic, so why not just let me help him with it."

"Help him?" Cas scoffed. "Like how you helped him last time? He went and murdered people Crowley. You couldn't even keep a leash on him."

The demon clenched his jaw and stood up, dusted off his suit and went to leave. "I'm assuming Moose did something to keep me out of that room. But don't worry, I'll be back." With that, he disappeared.

_Man, Crowley liked to hear the sound of his own voice._

_…._

Castiel appeared at the end of the hallway, opposite of the room Dean was in. The angel started down the hallway only to stop in his tracks. The door was left wide open and there was a can of paint spilt on the floor. Cas rushed down the hall and saw the crossed out demon sigil. Somehow he knew what he'd find, but he checked anyways.

Walking in, Castiel saw the chains on the floor next to the empty chair.

_Dammit Dean, what did you do?_

"Sam? SAM?" Cas searched the whole bunker but couldn't find a trace of the younger Winchester. Had Dean taken him? Is he even still alive?

The angel decided the quickest way to find both the Winchester's was to get help from his angels. Hopefully they'd still be willing to help.

…

"Are we there yet?" Dean said with a smirk. "I have to pee."

"Demons don't pee. Now shut up." Sam said, sighing heavily. Dean hadn't stopped talking since they had left the bunker two hours ago.

"But Sammyyyy" He whined, making sure to drag out the 'y' as long as he could.

"I'm not afraid to gag you Dean."

Dean gave a slight laugh and his eyes had returned to green. "Can you at least tell me where we're going? The suspense is killing me. I need to know if I should be prepared for pain."

"Bobby's. We're going to Bobby's house." Sam said casually.

"That might be a little difficult seeing as though it burned down years ago." Dean said glancing at his brother. _Maybe he has gone crazy. I'm stuck in a car with a crazy person._

The hunter saw Dean's judging face from the corner of his eyes. "I know. But the yard is still there and I have an idea."

"Care to share with the class?"

"Nope." Sam said, turning up the music.

With that Dean shut up, knowing he wasn't going to get an answer out of his brother since he willingly turned up Metallica.

….

After driving for thirteen straight hours, Sam needed a break. He was hungry, tired, and had to pee so bad he thought he was going to explode.

Finding a nearby motel, he went in and ordered a room, keeping Dean in the car.

Fidgeting with the cuffs, Dean desperately tried to find a way out of them. He had ditched his lock picks a month ago and now was regretting it. _Maybe if I yanked hard enough…_

Sam walked out just in time to see his brother trying to yank the handle off from the car. Getting in the driver's seat, he looked over at Dean who looked like he just got caught with his hand in a cookie jar.

"I had an itch." The demon said with a sly grin. Sam put the car in drive and drove around to where their room was.

"Now you have two options, either you sleep in the trunk or you can go inside and behave yourself." Sam said defiantly. He was not in the mood to deal with his brother's bullshit.

With a heavy sigh Dean mumbled 'room' as Sam got out of the car. Moving to the passenger's side, he took out the key and undid the cuffs that attached the eldest Winchester to the door handle. Dean got out of the car and with Sam having a firm grip on his arm, walked towards the door. As soon as his little brother unlocked it, he shoved Dean into the room, locking the door behind them.

….

"Hannah I need your help." Cas begged. He knew he didn't have the right to ask, but prayed the angels would find it in their hearts to help him.

"_You _need _our _help? Where were you when we needed a new leader Castiel?"Hannah looked pissed. They still hadn't found a leader. Maybe if Castiel took the job… she might be more willing to help.

"I'll do anything. It's of great importance that I get help."

"What's so important?" The angel asked curiously. Something had Cas in a frenzy.

Cas had to stop and think. Could he tell her about Dean? "It's… Dean Winchester. I need help locating him but he's warded himself from angels."

Hannah rolled her eyes. "The human again. Castiel he is just dragging you through the mud."

The angel could only see one way to get help from them, so he told them everything. What had happened once Dean woke up, what Alastair and Crowley did to him. _What I did to him. _

Hannah sighed heavily. Then, after a few moments of thought, "We will help-"

"Thank you so mu-."

"_IF, _you lead us."

Castiel just slowly nodded his head, hoping that this time, he wouldn't go insane.

…

**TBC**

**Please keep up the nice reviews! They make my day!**


	11. Chapter 11: Weekend At Bobby's

**CHAPTER ELEVEN: Weekend at Bobby's**

Dean walked in and plopped himself down on the bed. He really needed a shower but doubted Sam would let him.

Sam was eyeing his brother's wrists and cringed. They were bloody and blistered from the cuffs digging into them and he was unable to heal himself.

"Take a picture, it'll last longer." Dean said as he readjusted the cuffs. He remembered how the angel blood has caused him to have something along the lines of seizures, but he wouldn't tell Sam that. He refused to let his brother know how powerful the blood was against him.

The hunter walked over slowly to Dean, and loosened the cuffs slightly, hoping to alleviate some pain.

Neither of them said anything for awhile until Sam couldn't take it anymore. "Man, you smell."

Dean rolled his eyes, "Sorry, haven't had a chance to shower since you guys nabbed me." He said with some venom in his voice.

Sam's heart ached as he watched his brother's eye switch back to black. "Go shower."

"What?" Dean said, obviously surprised.

"Yeah, there are no windows in there so you wouldn't be able to leave. The cuffs have to stay on though."

The eldest Winchester nodded as he went to the bathroom to wash up.

Sam then proceeded to draw demon and angel warding sigils all over the walls, hoping to keep them under the radar.

….

"Castiel, we can't necessarily find them, but we did find a heavily warded motel room." Hannah said, gesturing at the paper map. "It's in Sioux Falls."

Cas eyebrows furrowed. _Sioux Falls? Wasn't that where Bobby lived? _The angel nodded to himself positive that's where the brother's were held up.

"Thank you Hannah. I'll be back as soon as I am able."

"Castiel wait, do you want some help? He sounds dangerous." The worry was evident in Hannah's voice.

"Dean wouldn't hurt me." Cas said with the utmost confidence. Hopefully, he wouldn't end up eating his words.

….

Dean was jolted awake by someone jerking his shoulders. His reflexes took over and he pulled his gun from under the pillow and aimed it at the attacker.

"Whoa whoa! Calm down. It's just me. Wait, where'd you get that?" Sam said, confused as to 1) why Dean felt the need to have a gun and 2) why he was sleeping.

"I may have snagged it from your jacket." The youngest Winchester snatched the gun away from the demon and put it in his waistband.

"Why were you sleeping and why were you sleeping with a gun?" Sam asked curious.

"Old habits die hard I guess." He said with a shrug. "And just because I don't need to sleep, doesn't mean I don't want to." Dean said smirking. He started to stretch only to get resistance from the cuffs. Sighing heavily, he got up to put his shoes on. "I'm assuming we're heading out?"

"Yeah, I feel like we've been here too long. Better be safe than sorry." Sam stopped before asking, "Do I have to drag you out or can I trust you'll just get in the car?"

"My middle name is trust-worthy." The eldest Winchester said with a sly grin.

Walking out of the motel room, Sam still kept close to Dean, but didn't grab a hold of his arm. After he got into the car with no problems, the hunter hesitated before reapplying the cuffs to the door handle.

"Is this really necessary? Come on, Sammy. I thought we bonded. Ya know, first road trip in awhile." Dean's eyes were back to black which was the main reason Sam had put the other cuffs back on. He still didn't trust his brother as far as he could throw him.

Getting in the driver's seat, Sam drove away only missing Castiel by three minutes.

…

By the time Castiel had gotten to the motel room, he was too late. The boys had left the curtains to their room wide open so all the angel had to do was glance in the window.

The room was clean, not even a sock left on the floor. _The Winchester's obviously weren't here. _If they had been there, they weren't anymore. Testing a theory, Castiel disappeared after making a quick glance around the parking lot for the Impala.

…

Sam pulled into Bobby's old car yard and blinked back tears. They hadn't been back here ever since it burnt down and the youngest Winchester had never really grieved properly for the old drunk.

Hoping being back here was having the same effect on Dean, the hunter glanced over and saw his eyes kept flickering back and forth from black to green. Sam smiled a little taking it as a good sign.

"Come on, let's go." Sam said gesturing for Dean to get out.

Dean was giving Sam the biggest bitch face he possibly could as his brother went around to undo one set of the cuffs. Laughing a little, he grabbed the demon's arm yanking him out.

"Um… I'll stay in the car." Dean said, trying to get his arm away from Sam.

"I don't think so." Sam said the tone in his voice daring Dean to try to run.

Having to half drag Dean to the center of the yard, he finally stopped at a huge ring of ash. Over the years, some had blown away, but there was still enough there to signify the spot.

"Do you know what this was?" Sam asked, eyeing his brother closely.

Dean took a deep breath and let it out slowly. "Yeah Sam, I do. So what? Was your plan to bring me here and watch me break down and cry?" He laughed a little but the hunter could tell that his brother forced it. "Hate to disappoint you Sammy, but I grieved enough for Bobby when I was human."

"For fuck's sake, Dean! This is where we cremated him and you're going to try to tell me that not a single emotion is going through that goddamn head of yours?!" Sam shoved his brother against a car, holding on to the front of his shirt.

"Not a one." Dean said with a smirk. His eyes had been solid black for a minute now and a twinge of doubt went through Sam.

"You're full of shit Dean." Sam said as he shoved his brother away from him.

"Sorry Sammy, don't blame me for your plan not working."

Sam scoffed, "I know you enough to know when you're faking Dean. The way you forced a laugh and how you didn't want to get out of the fucking car is enough to say you're feeling something. Don't lie to me. You at least owe me that."

"I _owe _you that? That's rich. Tell me why I owe you again?" All of a sudden the demon got serious. His eyes went back to the brilliant green color and he was leaning against the car his brother shoved him against.

"Should I go more recent? How about letting a damn angel possess me?" Sam spat. He had been keeping this in for awhile and now that he started, he doubted he'd be able to stop.

"I think we got even when you guys started the torture. I didn't want to become this. I told you that with my dying breath I didn't want to be what the mark was turning me into. Yet did you have the balls to kill me? Of course not." The venom in Dean's voice was evident and his eyes switched back to black. He was going deeper in the pit of his soul, and if Sam didn't act soon, would be even harder to retrieve.

Before the argument could get any more heated, Castiel appeared between the two brothers.

"Cas it's not what it looks like-" Sam started.

Before anybody saw it coming, Cas picked Dean up and tossed him into a car.

...

**TBC**

**Please continue to leave such great reviews! You guys are the bomb. What's going to happen with Dean's humanity? Is he ever going to be Sam's protective older brother ever again? We'll see:)**


	12. Chapter 12: Baby Steps

**CHAPTER TWELVE**

Struggling to get up, the angel appeared in front of the demon and kicked him in the ribs, forcing him back to the ground. "If you knew what's good for you, you'd stay the fuck down." Castiel said, obviously pissed.

"Cas stop! I let him out! I brought him here!" Sam pleaded, grabbing Cas by the shoulder.

Looking down at Dean coughing up blood, the angel backed away from him. "I-I'm sorry Dean." Cas sputtered, noticing how the demon hadn't even attempted to fight back.

Helping Dean up, Sam unlocked the cuffs so his brother could at least heal himself from Cas's tirade.

Instant relief flooded Dean's face as he slowly started to heal himself. The blisters on his wrists started to disappear and Sam could see the creases in Dean's face relax.

"Good to see you too, Cas." Dean spat. Looking healed enough; Sam put the warded handcuffs back on, causing a groan from the demon.

"Sam, would you care to explain why you are working with _that_?" Cas hissed. He couldn't believe that the youngest Winchester had teamed up with the demon. _Nothing good ever came from that. _

"Dean, go get in the car." The hunter ordered obviously not wanting his brother apart of the conversation.

"I can take a hint." The eldest Winchester said with quick glare at Cas.

Once they saw Dean get in the car, Sam turned to Castiel.

"Listen, I have a plan-"He started.

"Sam nothing good has ever come from working with demons. You know that." Castiel said shaking his head.

"Don't you dare throw Ruby in my face! This is different. Besides, does it look like I'm working with him? Hell, I had to drag him out here. He's cuffed Cas and he can't do a damn thing." Sam then remembered hearing his brother's screams when they tortured him with the angel blood and cringed. "I couldn't do it anymore. I had to try something else and it's actually working."

"What exactly are you doing?" The angel asked, his voice softening. The hunter could still see how tense his shoulders were and could tell how much he didn't like this.

"I'm trying to touch into his humanity. When we first got here, he couldn't keep his eyes black, they kept flickering back and forth. We started to make progress but then he said some smart ass comment and I lost it. Either way, he was like normal the whole way here. It's working Castiel. I just need some more time."

"There are plenty of people after him. And now the angels know as well what he is. I'm sure hunters will soon follow." Cas said, regretting telling them about Dean's recent change.

"They what, Cas why did you tell them?" Sam said in disbelief. He threw his hands up and wiped a hand down his face. "Just add more things to the list of people after Dean."

"Sam I-"The angel started to apologize but Sam wasn't having it.

"No Cas its fine. Just, I got to go. We've been here too long." Making his way to the car, the hunter got into the driver's seat without adding the extra cuffs to secure Dean to the door handle.

The Impala pulled away, leaving Castiel standing there regretting everything he had done since they rescued Dean from Alastair.

…

Crowley was sitting in his swivel chair in his office, when a knock came from the door. "Come in" The King said lazily.

"Sir, we have the whereabouts of the Knight." His demon recruit stated.

Crowley sat up straighter, his attention caught, "And? Come on, elaborate. I don't have all day."

"He was just spotted leaving a car yard in Sioux Falls _with_ Sam Winchester." The demon stepped closer to the former crossroads demon.

"Keep tracking him. Don't lose him. Oh, and let Alastair know that his favorite pet will be back soon."

"Actually Sir…"

"What? Spit it out!"

"Alastair wanted to go with you. He said he didn't trust you with his precious cargo." The demon said hesitantly.

The King rolled his eyes, "Fine, send him word of your findings."

With that, the demon left leaving a smiling Crowley to begin to plot.

….

After driving for two hours, Sam couldn't listen to his stomach growl anymore. Stopping at a local diner, he undid Dean's cuffs.

"Are you sure about this? You could just tell the waitress were KLARPing." The demon said with a smirk.

"It's LARPing… I think. Either way, I'm not going to try and explain these." He said holding up the cuffs. "Just please, don't make me regret it.

Putting his hands up to show he meant no harm, he made his eyes switch to green and walked in.

"You boys can sit anywhere you like!" The perky waitress with the just as perky boobs said.

After taking a glance at the waitress's ass, Dean went and sat at a booth. Sam smiled to himself believing he was getting closer and closer to getting his brother back.

"What can I get you boys?" The hostess asked, who Sam noted name was Jenn.

"Coffee. Black." Dean said handing her the menu.

"I'll have a caesar salad. Thanks." Jenn smiled at them and walked back to get Dean's coffee.

"So-"Dean stopped talking when two middle-age gentlemen stood at the end of their table.

"Hiya Dean, Sam." The taller one of the two said.

Sam looked at them questioningly. "May we help you?"

"We were wondering if we could talk to you outside, mainly Dean." The taller man said, seeming to be the leader of the two.

"Man, any other time we would. But, see, we just ordered our food and need to get back on the road." Dean said his words laced with sarcasm. Looking at the other one's hand, he could see him holding a flask with a cross on it. _No doubt holy water. _

"It'll take no more than a minute." He said persisting.

"Maybe you didn't quite understand me, fuck off." Dean hissed.

Jenn then chose that moment to come back to the table and sat down Sam and his order. "Will you two be joining them?"

Before one of them could answer, "No, they're just visiting for a moment." Sam clarified.

After waiting for the waitress to walk away, the two obvious hunters glared at Dean. "Don't have the balls huh?"

Dean laughed and shook his head "No, trust me; I could kick both of your asses with one hand tied behind my back."

The taller one raised an eyebrow doubting Dean could touch them.

"Fine." Getting up, Dean made his way to the door with the two men following. Sam hurried behind them, so he could have his brothers back.

After making their way behind the store, Dean immediately flung them both against the back of the building.

"I'm assuming you guys heard of me as a hunter. Let me tell you, I was a great hunter, you don't want to know what I'm capable of as a demon." Dean walked over in front of the taller hunter and stopped with their noses inches apart. "If you value that pathetic little life of yours, I suggest you get the fuck away from me." With that, he let the two hunters down and they both landed on their knees, clearly fuming.

"This isn't over!" The leader said as he and his partner ran off.

"Dicks." Dean said looking over at Sam.

"They're just doing their job." The youngest Winchester said. _So will all the others that will come. _

Shrugging, the demon went over to the car and slid into the passenger's seat with his brother slowly following.

Dean held out his arms waiting for the cuffs. When Sam hesitated, "Come on man, do it." He practically pleaded. His eyes had gone back to green once he got back in the car.

"I don't need to." Sam said turning the car on.

"I need you too. Please, just… Just do it." Dean wouldn't look at his brother. He just waited with his arms out hoping Sam with get on with it without making a big scene.

After a moment of thought, Sam put the cuffs on and drove down the road.

….

**TBC**

**You guys are literally perfect. Thanks so much for all the reviews. If there's anything specifically you want to read about, let me know!**


	13. Chapter 13: Anyone's Game

**CHAPTER THIRTEEN: Anyone's Game**

Because Sam still refused to talk to him, Dean decided to nap; or at least try too. His brother hadn't said a single word to him since they left the diner and it had been a solid fourteen hours. Hell, he was wondering how Sam was still able to drive.

Resting his head against the window, Dean closed his eyes.

….

_Dean was running through the woods. Not a calm light run, a run-for-your-life kind of run. Glancing over his shoulder, he saw the whole gang after him. Some of the faces he could make out ranged from Sam, Crowley, and Alastair, to Castiel, other hunters, and even his goddamn dad. _

_He'd been running for hours dodging roots and fallen branches. He glanced back again and saw they had cut Dean's lead by half. Every time he would look they'd be even closer. Finally, he tripped over a protruding root and fell face first. _

_The last thing he remembered was Sam and his dad looking over him smiling, right before Cas jammed the angel blade through his heart._

…

Dean awoke with a start and accidentally punched Sam in the arm.

"Hey! Dean it's me! You're okay!" Sam yelled. He had pulled the car over to the side of the road once the demon had started screaming.

Blinking away his confusion, Dean looked over at Sam with those dazzling green eyes. "Sorry, I um, muscle spasm." He turned his head to look out the window, hoping his brother wouldn't pry.

"Yeah, because muscle spasms include screaming while you sleep." Sam said rolling his eyes. He put the car in drive and continued down the road.

"Damn straight." Dean said his usual sarcasm returning. He ran a hand down his face, and tried to rub the sleep from his eyes.

….

"Castiel, I didn't expect you back so soon." Hannah said stepping away from Metatron's old desk that now belonged to Cas.

"Change of plans." He said shortly. The angel wasn't in the mood to deal with all her questions. He turned his back to her and ran a hand through his hair.

"Sir, I think we should send a team down. Maybe we could take care of him-."

"No. He is being taken care of." Castiel said, turning to face the angel. Sometimes he wished she didn't have such a stick up her ass.

She nodded firmly and left Cas to his thoughts.

For the first time in years, the angel prayed. He prayed for Sam and Dean's safety, he prayed for Dean's humanity, he prayed for his fellow angels. After he had finished, Castiel laughed at how ridiculous he was being.

Dean Winchester was making progress and that's all he could ask for.

…

Crowley was looking around the bunker for any signs of how they got Dean to scream so loud. After all the torture Alastair had done, he hadn't once elicited quite a response. Walking into the dungeon he knew too well, he walked over to the IV bag that was left there.

The King put a finger into the bag, wiped the side of it, and licked the blood from his finger. _Angel blood. _How could he have been so stupid? It was all so obvious now.

All he needed to break Dean Winchester was a few ounces of angel blood.

….

Crowley tossed the lifeless body to the side. After draining the angel of their blood, he had no use for the body. Carefully placing the last bag full into a cooler, he picked it up and carried it down the hallway to the room where they were once keeping Dean.

He pulled out a few syringes and proceeded to fill them with angel blood to use when they found the Knight. Alastair would be pleased to finally find a way to hurt the smug bastard known as Dean Winchester.

Alastair walked into the room, closing the door behind him. "Got your message. What's so important?"

"What would you say if I told you I found a way to wipe the smirk from Dean's face?" Crowley said gesturing towards the cooler.

"You've got my interest." Alastair said as he glanced inside the cooler and took a deep breath in. "Angel blood, why we hadn't tried this before is beyond me."

"I've got a plan. Care to run an errand?" The King smirked as Alastair turned and walked out the door, chuckling to himself.

….

**TBC**


	14. Chapter 14: The Tables Have Turned

**CHAPTER FOURTEEN: The Tables Have Turned**

The brothers had only been driving for half an hour when the King of Hell appeared in the back seat of the Impala.

"Hello boys."

Sam veered and almost hit another car from the shock. Pulling off to the side of the road, the youngest Winchester put the car in park and the brother's both got out with Crowley following. Sam stood protectively in front of Dean. He then glanced inside the car and saw the handcuff key left on his seat. _Fuck._

"Nice of you to have him packaged for me." The King said, glancing at the cuffs.

"You're not taking him Crowley." Sam hissed. He'd be damned if he let it happen a second time.

All of a sudden Dean turned around only to have his jaw meet Alastair's fist causing him to stumble backwards. Closing the distance between them, the eldest Winchester was knocked to the ground by a kick to his ribs. Crowley decided to then send Sam flying over the Impala to the other side of the road.

"Dean, long time no see." Alastair said with his usual malice, glancing down at Dean. Before he could administer another kick, the hunter swung his legs around, knocking Alastair to the gravel. He then proceeded to scramble over on top of him, putting his hands around Alastair's throat.

Sam slowly got up from where he had landed and ran over to Crowley, drawing the angel blade. Lunging at him, the King side-stepped, causing Sam to stumble forward. The King of Hell walked over to his Knight and put him in a choke hold dragging him off of Alastair and a few feet away from his brother. Desperately clawing at Crowley's arm, Dean could feel himself losing consciousness.

"Let him go." Sam hissed.

"Sorry Moose. I'm not letting my biggest investment just roam free. I've got big plans for him and you can't stop me." With that, Crowley took out a blood filled syringe and jammed it into Dean's arm. The effect on his brother was almost instantaneous as all the color drained from his face. Dean went limp in Crowley's arms and he let go, the demon hitting the ground hard.

Before Sam had time to react, Dean was convulsing on the ground almost like a seizure.

"Crowley, you son of a bitch. Leave before I kill you." Sam spat, ripping his attention from his brothers twitching form.

"Come on Moose. Be real." The King of Hell snapped his fingers and both him and Dean were gone, with Alastair following after sending a smirk Sam's way.

Sam decided having your brother taken away from you is much more painful the second time.

….

Dean woke up very confused. He refused to open his eyes, but was confused as to why he was on the ground and not restrained on Alastair's rack.

Prying his eyes open, he looked around to see he was in a room made of pure iron with the demon warded cuffs even more tightly attached to his wrists. There were no windows or furniture in the room, just one solid door with no handle on the inside.

Slowly standing up, Dean pressed his ear to the door, seeing if he could hear anything. After hearing absolutely nothing, he turned around and ran a hand through his hair.

After what seemed like an eternity, the door swung open and Crowley walked in with a full syringe in his hand. The eldest Winchester took a few steps back putting his heads out to fend off the King.

"Can't we at least be professionals about this?" Crowley said putting his empty hand in his pocket.

"Where am I?" Dean spat.

"We decided Hell was too obvious of a place to take you. So we settled for this smelly dump until more… permanent arrangements can be made." The King said, obviously thinking he won.

"Sam's just going to come find me again." The demon said letting out a shaky laugh.

"Oh I don't doubt it. But see this time; we won't even give him enough time to say two words. He'll be dead before he walks through that door." Crowley said, pointing to the door he had just walked through.

Walking over to Dean, the King grabbed the chain with his empty hand that attached the demon's two wrists, yanked down, and plunged the syringe into the Knight's neck with his other.

Dean fell to the ground and seized. Smiling with satisfaction, Crowley left the room and locked the door behind him, leaving Dean to suffer alone.

….

**TBC**

**Sorry these two chapters have been kinda short! Let me know if this story is being dragged out too much. I don't really know what the appropriate amount of chapters for something is. Please continue to leave such nice reviews, they make me so happy.**


	15. Chapter 15: A Prayer Or Two

**CHAPTER FIFTEEN: A Prayer Or Two**

Eight weeks.

Dean had been taken eight weeks ago and Sam had lost all hope of finding him. He had tried every locater and summoning spells in the book and not a one had worked.

Not to mention Castiel had gone MIA. The youngest Winchester doubted he even knew Dean was missing. Ever since the Bobby incident, the angel had kept his distance probably embarrassed about the whole thing.

Sam had tried praying to Cas at least three times a day, and now was his normal time to do it for the second time. But he decided to try something different.

_If any angel at all can hear me… _He laughed slightly. _Um… It's bad. Crowley and Alastair took Dean. Like two months ago. I've tried everything and well… it seems hopeless. Your angel mojo would be pretty helpful right about now. If anyone is willing to help… Having a Winchester in your debt might come in handy._

With that, Sam continued flipping through one of the many books in the bunker's library. But the hunter couldn't focus, his mind kept turning back to what the hell was happening to his brother.

….

After what had happened the last time he saw Dean, Castiel decided it was best to stay in heaven. He obviously didn't know the best course of action to help his friend so he left the job up to Sam.

But something kept itching at the back of his mind. He had flipped off his angel radio about two months ago because he felt he needed to focus on maintaining heaven.

Knocking tentatively on the door, Hannah walked in. "Sir, there's something you might want to know."

Standing up, he walked over to the angel sensing something was troubling her. "What is it?"

"It's Sam Winchester. He just put out a prayer to every angel and its upsetting news." She hesitated before continuing, "The King of Hell and Alastair have managed to recapture Dean. Apparently it happened two months ago."

Castiel cringed. How could he have been so stupid? "When did he put this prayer out?"

"About ten minutes ago, Sir."

"Hold down heaven while I go check things out." Not giving her a chance to respond, Cas disappeared hoping to right some wrongs.

….

Deciding not to put Sam in danger, Castiel set out to find Dean by himself.

He started by searching Hell, only to come up empty. He figured there was no possible chance of Crowley bringing him back there, but he had to make sure.

After convincing Hannah to search for heavily warded areas across the United States, he went to the bunker but didn't allow Sam to see him.

The youngest Winchester was slouched in a chair, pouring over some book that wasn't going to help. Castiel's heart ached as he watched the hunter try to focus.

He received word shortly after about 20 possible hits of where Dean could be, most being regular American houses. Deciding Crowley wouldn't keep a rogue demon there, he narrowed the search.

Four possible abandoned factories where all that was left by the time Cas had stopped narrowing. Setting out for the first one, the angel sent out a silent prayer that he wasn't too late.

…

It had been six weeks of seizures and two weeks of intense, blinding pain before Crowley began to figure out Dean was growing a tolerance for the angel blood. The hunter was pacing the room back and forth and crossed his arms across his chest. Any color the demon had was gone. He was sickly pale and had a fever of 103 degrees most days. His finger nails were bitten to nubs and his wrists were so badly worn, you could practically see the muscle underneath the skin.

Sure, it still hurt like a bitch whenever he was injected with the stuff, but not nearly as much as week one. The more injections, the more human he felt. Of course, Dean didn't tell Crowley that. He knew that if he was going to get out of here, he'd need to con the King of Hell. Easy.

"Dinner time, squirrel." Crowley said as he walked into the room, making sure to shut the door behind him. Dean craned his neck, hoping his cooperation would put him on good terms with The King and he could get out of this shit hole. The demon eyed the eldest Winchester carefully as he plunged the needle into his neck and pressed. Dean immediately began screaming and cradled his head in his hands as he fell to the floor. Crowley smiled satisfied with himself and left.

An escape plan was forming in Dean's mind and all he needed was one more visit from Crowley.

…

Cas only had one more factory to explore, and from just looking at the outside of it, he was pretty damn confident this was the place. Demons were spread out along its perimeter and they all had angel blades in their hands, obviously ready for anything.

The angel could see warding sigils plastered everywhere and knew he was going to need some help in order to get in to save Dean. After fighting with himself, he disappeared to go and get Sam, knowing the hunter would want to take part in his brother's rescue.

…

**TBC**

**I'm hoping to wrap this story up by chapter 18 or 19 maybe? We'll see how things go. Thanks so much for reading and reviewing. It means a lot!**


	16. Chapter 16: A Plan In Motion

**CHAPTER SIXTEEN: A Plan In Motion**

Dean was surprised by his door creaking open in the middle of the night. Normally he got his visits three times a day, which was already over with.

He didn't think he could hold on for much more.

He knew how much easier it would be if he just let his humanity fade away. Hell, he's dreamt about it. But every time he's about to do it, his mind comes to Sam and Castiel and he can't make himself just let go.

He's not done protecting Sammy yet.

So when Crowley walked in the door, he wasn't able to perform his escape plan. He'd have to wait until his next visit.

"Care for a middle night snack?" The King said, holding up the glass syringe that Dean cringed every time he thought about.

"You said you had plans for me Crowley. How much longer are you going to drag this out before you tell me?" Dean spat. Hopefully, the ruder he was, the less humanity Crowley thought he had.

"All in good time Squirrel, all in good time. For now," He walked over to his Knight and poked the needle into his neck and pressed down on the plunger. Dean crumpled to the ground and had his first seizure in two weeks. "Sorry about that, I decided to up the dosage. Seeya in a few hours."

Crowley walked out and purposely slammed the door behind him. Dean's head was pounding as he seized on the floor, unable to stop the silent tears that fell down his cheeks.

…

"Sam." Castiel said, appearing right next to the researching hunter.

"Cas? Man, personal space." The youngest Winchester said as he slowly stood up, stretching.

Taking a few steps back the angel started again. "I've located Dean. However-"

"Wait, I didn't even know you were looking for him let alone knew he was missing." Sam said obviously confused.

"Hannah told me of your prayer. I had turned my angel radio off and had not heard it. I then immediately came to earth and began searching and found him. By the looks of it, he's heavily guarded."

"Cas hold on. You're giving me a headache." The hunter began rubbing his temples as he spoke again, "So when you turn off your angel radio, you can't hear prayers anymore either? That's… I mean at least I know you weren't just ignoring me all this time."

They both were silent for awhile, neither of the two wanting to say what the other was thinking. But then, Sam finally said it.

"Do you think he'll be… gone?" The youngest Winchester said with obvious pain in his voice.

"Your brother has surprised us before. He's surprised me in the past few weeks. He'll pull through Sam. But, we got to get moving before it's too late."

….

This time Dean was ready for Crowley's next visit. The hunter waited right by the door, and the second he opened it, grabbed the King's coat, dragged him inside and left the room making sure to lock the door behind him.

As he slowly made his way down the hallway, he could just barely hear the faint knocking from Crowley. Taking another step, the realization that he was free (almost) hit him and a small smile crept on to his face.

Making his way down the hallway carefully, he cursed when he realized he was 1) powerless and 2) weaponless. _Fucking cuffs will be the death of me. _He thought as he glared down at them.

He peaked around the corner and immediately pressed himself against the wall he was originally on. A whole mass of demons was making their way down the hallway, right where Dean was hiding.

_Shit, shit, shit. I'm so fucking screwed._

Dean looked around and could only find one other door, so he went for it. He opened and closed the door behind and sunk to the ground with his back up against the door.

When he looked up, he saw a demon glance up from the desk and jump up once he saw him. _Shittt. _Scrambling to his feet, Dean somehow managed to get the demon underneath him, with the angel blade the demon had been using, up against its throat.

"Do you know what Crowley has planned for me?" Dean spat. He wanted answers and he needed them fast.

"Only he and Alastair know. Something about the King having trust issues." The demon smirked. Oh man was Dean going to gut this bitch.

"Quickest way out. Now." The eldest Winchester barked.

"Kill me, I won't tell you."

"If you insist." Dean's smug smile returned, his eyes going black as he jabbed the knife up through the demon's jaw.

….

**TBC**

**Keep the reviews coming, you guys are fantastic!**


	17. Chapter 17: The Great Escape

**CHAPTER SEVENTEEN The Great Escape**

Dean stood up from the lifeless body and glanced around the room. Eyeing a computer, he walked over to it finding it to be password protected. _Where's Sammy when I need him._

Walking out of the room, the demon glanced down the hallway where he had been held and saw his cell door was wide open. _There goes my upper hand. At least I have a damn weapon._

Just when things were starting to look up, a deafening alarm rang out from the speakers. Element of surprise forgotten, Dean ran down the hallway and made a quick right, taking a sigh of relief when he noticed the hallway was empty.

Trying to navigate a building you've never been into and trying to find exits you've never seen, proved to be more difficult than the eldest Winchester predicted.

Deciding he might as well go out with a bang, he set out to find Crowley.

….

Castiel and Sam appeared on top of a hill that overlooked the property. With closer inspection, all the demons the angel had seen earlier were gone.

"I thought you said it was heavily guarded." Sam asked, worry creeping into his voice.

"It was. Listen." They could hear a faint alarm going off from the factory.

"Something tells me we better hurry." Sam said as he ran down the hill to the nearest door. After yanking the door open, the youngest Winchester stood in the doorway waiting for Cas to come on.

"I can't Sam. There are too many warding sigils. You go ahead and get Dean. I'll be out here waiting for you."

The hunter hesitated before going inside. He knew his brother's life was on the line and he refused to let him die.

_Now it's my turn to do the protecting. _

…...

Dean was only able to run so far down the hallway before the little strength he had began to dwindle. With the cuffs still on, he had no way of healing himself.

The eldest Winchester walked through a door that lead to a huge open room. There were conveyor belts and packaging stations spaced evenly throughout but were too rusted to even work. He slowly made his way around the edge of the room when he heard a familiar British accent yelling at people. As he gradually inched closer, the words became more defined.

"What do you mean you haven't seen him? He's one bloody demon and you all are saying you can't find him?" Dean could practically see the scowl that was firmly placed on the King's face.

"Sir, he's obviously found a way to evade us. But he is still wearing the warded cuffs, so he won't be able to get very far." One demon spoke up. _Someone's about to piss themselves._

"I want him found. And I want him found now. Think you lot can handle that?"

"Yes Sir." Just like that, they all took off in opposite directions. Dean quickly ducked behind a pile of boxes trying desperately to stay quiet.

….

Sam had been snaking his way through hallways for a solid five minutes before he started getting aggravated. He had been dodging demons that seemed to travel in huge ass packs that would occasionally mutter something about Dean escaping.

The hunter just peaked over a wall when of all things, his cell phone rang. Desperately trying to get it out of his pocket to try and silence it, Sam cursed under his breath. Turning his phone off to prevent another interruption, he turned the corner and ran into Alastair himself.

"Sam, I was wondering if you could help me with something."

Before the youngest Winchester could do anything, Alastair rammed his head against the wall. Sam's vision blurred as the demon yanked him up by his hair, and dragged the hunter down the hallway.

….

Just as Dean was about to go confront the now alone King, the doors closest to Crowley burst open and none other than Alastair walked in, dragging Sam in by his hair.

_No Sammy no. I don't need rescuing._

"How about we make a little announcement?" Alastair suggested.

The King made his way over to a telephone that broadcasted anything spoken into it throughout the whole factory. Although it wasn't needed seeming as though Dean could see the whole scene unfold right in front of him. _Dammit Sammy._

"Dean, I believe we have something of yours. But we're willing to trade little Sammy's life for your cooperation. Clock's ticking." Crowley hung up then phone and walked over to Sam.

"You screwed your brother over Moose. I bet he could've gotten out of here if he didn't have you to protect. But who knows, maybe enough of his humanity is gone; he won't give a shit about you."

Dean's heart ached as he saw Sam stand there with blood trickling out of his nose, not saying a word.

With a deep sigh, Dean walked out from behind the boxes. "Alright Crowley you son of a bitch," the eldest Winchester's breathing was coming in short little gasps now as he struggled to keep himself up right. "Let Sammy go."

Crowley eyed Dean with a sense of betrayal. The King had really thought that the hunter's humanity had all but vanished.

….

**TBC**

**I don't know if I want this to be a happy or sad ending. Let me know? I'm kinda leaning towards sad. We'll see.**


	18. Chapter 18: Our Choices Define Us

**CHAPTER EIGHTEEN: Our Choices Define Us**

"I got to say Dean, I'm disappointed. You were finally starting to get some good qualities." Alastair said smugness evident in his voice.

"I. Am. Not. Speaking. To. You." Dean said each word through clenched teeth, and returned his attention back to Crowley. Surprisingly, Alastair shut up.

"A bit moody are we?" The King asked, taking a step towards the eldest Winchester.

"Let Sammy go. I won't ask again." Dean was having trouble keeping himself upright. He hadn't been able to heal himself and because he was so close to returning to his human state, his strength was almost nonexistent. From all the extra movements, the cuffs had buried deeper into his marred flesh, scraping away more and more muscle. His fever had spiked to 104 and his breathing was rapid. Sam eyed his brother worryingly, not wanting him to sacrifice himself for the umpteenth time.

"Dean. Listen to me. Don't do this." Sam pleaded.

The Knight acted as if he hadn't heard him. "You have me. My brother is useless to you. I'll cooperate. Just let him go." The words were forced. Dean hated for these bastards to win but he had no choice.

He had to protect Sammy.

Crowley snapped his fingers and two demons appeared, grabbing a hold of Dean's arms and shoulders. Alastair shoved Sam forward and backed away.

"Pleasure doing business with you." Just as Crowley finished, Sam pulled the angel blade from his inside coat pocket and stabbed Alastair in the heart.

"This time, I suggest staying dead." Sam hissed as he yanked the blade out and let the demon's lifeless body fall to the floor.

Catching the demon's off guard, Dean yanked his arm away from one and elbowed it in the nose, sending it stumbling back. Before the other had time to react, Dean took out the angel blade he had snatched earlier from the side of his waistband, and slit the demon's throat. Sam went after the other one, killing it just as easy.

Both the brother's whirled on Crowley, Dean's nostrils flaring and Sam clutching the blade with all his strength.

"Come on boys, you can't kill me without the blade. Seeming as though you don't have it with you, what's your plan here exactly?"

Sam tossed Dean a pair of handcuff keys to free himself as he pulled out another pair of warded cuffs from his back pocket. The cuffs that had been the cause of Dean's latest turmoil fell to the floor with a loud clank.

Acting fast, Dean flung Crowley against the wall as Sam walked over and cuffed him.

…...

Dean walked out of the bathroom, drying his hands off on a towel. Throwing the towel on the bed, he walked down the hallway into the bunker's kitchen where Cas and Sam were waiting.

A small smile crept across Sam's face when he saw his brother. He looked so much like he did before he got the mark, it was almost like it never happened.

But it did, and Dean did some awful things that will possibly destroy him. Even though Dean hadn't said anything, Sam knew his brother well enough to see the small signs he was stressed. The bags under his eyes, tense shoulders, straight back, and lack of appetite all were self-loathing habits of the hunter. The youngest Winchester didn't even know the extent of all the things his brother had done, but he could tell it was bad and that it was eating Dean alive.

"What are we going to do with him?" Sam asked, referring to Crowley who was locked down in the dungeon once again.

"We kill the son of a bitch. No question." Dean said, leaving almost no room to argue.

"Dean, the mark-" Cas started.

"I'm not letting that bastard go. Keeping him here is pointless, so he needs to be put down and I have to be the one to do it." The eldest Winchester held out his hand for the First Blade that was lying on the kitchen table behind Sam.

Sam hesitated and shook his head. "We can't go back down that road Dean."

"It's one demon. I'll be fine. Just please… Let me do this one thing right." Dean's voice was gruff as he tried to hide the guilt in his voice.

Sam reluctantly handed over the blade. Taking it, Dean made his way downstairs to the door of the dungeon and hesitated with his hand on the handle.

He was fighting with himself, the demon half versus his human half. Dean hoped his humanity would win in the end, but wouldn't bet on it.

Taking a deep breath, Dean walked in eyes going black.

…

**TBC**

**I can't decide whether or not to do a sad or happy ending, so I'm doing both (two separate chapters, but both ending the story). Not sure if it'll be the next two chapters or the two after. Please continue to review! Thanks so much for reading(:**


	19. Chapter 19: Too Good To Be True

**This is the sad ending. The next chapter is the happy ending. You can either read both, or one or the other. Whatever floats your boat.**

**CHAPTER NINETEEN: Too Good To Be True**

It may have been Dean who walked into the dungeon, but it wasn't Dean who walked out.

Maybe the guilt was too much or that last kill just sent him over the edge, but I had lost my brother. Again.

When we heard Crowley's screams, Castiel and I ran downstairs. It shouldn't have taken this long for Dean to just shove the fucking blade into his chest.

When we walked in, we weren't prepared for what we saw. The former King of Hell's head was on the opposite side of the room and Dean was covered in blood. What was left of Crowley's body was covered in gashes and stab wounds that were all oozing blood.

Dean's hand was shaking so violently that I was surprised he could keep a grip on the blade.

As my brother turned around, I could practically hear my heart break. His eyes were bitch black and he was smiling that wicked smile of his. He brought the blade up to his lips and licked some of the left over blood off and smacked his lips together.

"Ahhh, the taste of little bitch." The demon said as he wiped the remaining blood on his jeans.

"Dean what the hell-" Cas began saying.

The Knight cut him off with a hand motion. "Dean? Oh he's in here, but he can't play right now." He turned his gaze to me and smirked.

"You- You're not Dean." I stammered.

"Sure I am. I'm just the part he _tried_ to bury. Even if he hadn't killed Crowley, I would've just been dormant. I could've showed up years from now, but lucky for us all, I showed up today."

"Lucky?" I scoffed. "Try fucked."

"This way at least none of you have false hope of me ever getting better. Man," He laughed, "if you could've _heard_ some of the thoughts going through your older brother's head Sammy. It was a miracle he was able to stand with all the guilt he held. Even though he shouldn't have felt guilty for any of the things he did, he was just blowing off some steam." Taking a step forward, Dean patted me on the chest with his bloody hand.

I shoved him away from me as I yanked an angel blade from my waistband.

By this time, Castiel had gotten over the initial shock and was fighting ready. Drawing his own blade, he glared at Dean with determination.

This just made him laugh. With just an eye movement, he sent both of us flying against the wall. As I struggled against his power, silent tears fell down my cheeks.

My brother shook his head as he strolled over to me "Seeing as though nothing I could ever do to you would cause you any more pain than seeing me like this, I'll leave you two alive." Turning around, he made his way to Castiel "For now, I'm going to go take my place as the new King. Has a nice ring to it, doesn't it? I guess you've got someone new to lead that little angel army of yours against."

With that, Dean walked out of the room, the bunker, and our lives.

….

It had been three years since Dean had walked out of their lives, but I still had nightmares about that night, every night.

Not much had changed besides the fact that my brother was the one running Hell. The crossroad deals still happened, demons still walked the earth, and souls were still being tortured in the pit.

After three years, I couldn't take it anymore.

Without having my older brother there to steer me down the right path, I quit hunting and took up drinking as my full time job. After the first year, Castiel stopped visiting, probably from me telling him to get the fuck away every time he came around.

After three years, I was going to do something useful with my life.

I had no one else to live for.

Not mom, not dad or Jess, and not Dean.

So as I stood in the church, waiting to inject the last round of purified blood to cure a demon and shut the gates of Hell, I let out a sigh of relief.

After three years of pain and grief and self loathing, it would be over in a matter of minutes.

I didn't tell anyone I was doing this, not like I had anyone to tell. Everybody I would've told was dead or a demon.

So nothing to lose, right?

As I put the needle into the demon's neck, I pushed down on the plunger and immediately felt any strength I had left, leave my body I recited the final spell work, and collapsed on the ground.

Some people say that your life flashes before your eyes when you die. For me it was just a bright light, and then nothing.

I remember walking through the gates into Heaven and hugging everybody I had ever lost.

Mom, Dad, Jess, Jo, Ellen, Bobby, I could go on and on.

This is where my story ends, but I left behind a world safe from Hell, demons, and my brother.

….

**THE END.**

**For those of you that wanted the sad ending, there it was. The next chapter will be the happy ending, so if you want something uplifting, hit the next chapter button.**

**Thank you so much for making my first story a good experience. I'm already working up an idea for another story I'm going to begin writing shortly. So, if you enjoyed this story of mine, be prepared for more.**

**You guys are lovely.**


	20. Chapter 20: Happy Ever After

**This the happy ending. Hopefully you enjoyed reading my story.**

**CHAPTER NINETEEN: HAPPY EVER AFTER**

To be honest, I didn't expect Dean to walk out himself. Once we heard the dungeon door close, Castiel and I walked downstairs and waited by the door to see who, or what, came out.

When my green-eyed older brother walked out and handed Cas the blade, I couldn't help the tears that fell down my cheeks.

"Sammy, no chick flick moments." He said with a genuine smile on his face. Dean pulled me into a tight embrace, and kept muttering over and over again how sorry he was. I of course just shook my head and said he was crazy.

Dean turned to the angel and Cas was the one who initiated the hug. "Sorry for ever doubting you Dean." My brother let out a small laugh as he pulled away from him.

"Man, I could really go for a burger."

They all laughed as they walked down the hallway towards the Impala.

Tossing Dean the keys, the smile that crept onto his face was one that I would never forget.

After getting dinner and of course some pie, we made our way back to what would become our real home since before mom died.

…

The first few weeks after Dean had killed Crowley were rough. The most he was sleeping each week was five hours because all the nightmares were keeping him up at night.

Dean couldn't outrun the memories of what he did while he wasn't human and he constantly beat himself up about the horrendous acts he committed.

But we worked through it together, the three musketeers.

Every now and then Castiel would visit us when he wasn't too busy with things in Heaven. He and Hannah ended up getting together and Dean constantly gave him shit for it, good naturedly of course. This would of course just cause the angel to blush, which just gave Dean more material to make fun of the angel for.

….

Three years had passed since I got my brother back, and we couldn't be happier.

We got back to the basics of hunting.

We kept to Wendigos, ghosts, werewolves, and maybe the occasional demon, depending on how much Dean wanted to remember.

It was like what they did in the beginning, when Dean had changed their lives forever and snuck into his apartment he shared with Jessica.

His brother still had nightmares, but not nearly as many as he used to. But, when did they ever not have nightmares?

….

They were all sitting around the table together, Cas and Hannah, Dean and me, when I dropped a small box in front of my brother.

He looked at me with a confused expression as I gestured for him to open it.

After hesitating for a moment, he ripped open the box to then let out a small gasp of surprise.

Grabbing it by the string, Dean pulled out the amulet Sam had given him for Christmas when they were kids.

"Sammy, where did you get this? I thought I threw it away." He looked at me surprised, not believing what he was holding.

I shrugged casually, "I pulled it out of the trash. Figured I could give it back to you someday." I smiled as he put the necklace around his neck and clapped me on the shoulder.

"I never took you as the sentimental type Sammy. But I'm glad you kept it." He rubbed the amulet with his thumb as Cas launched into this huge story about when he had borrowed it and thought Dean was going to have a heart attack when the angel had asked for it.

Things were the best they had been in hell, nine years, and I couldn't ask for anything more.

….

**THE END.**

**There was the happy ending. I want to thank you guys again for reading and keeping up with my first story. I was so nervous when I first posted it, thinking no one would like it. You guys made my first experience on here great and definitely will be writing more. I already have a rough draft for the first chapter of a new story written.**

**You guys are fantastic.**


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